Classic Covers: The Art of Halloween

We rode our brooms back as far as 1913 to share original Halloween art with you.

Bobbing for Apples by J.C. Leyendecker

Bobbing for Apples by J.C. Leyendecker November 1, 1913

Before there were Rockwell covers, there was the great J.C. Leyendecker (a mentor to Rockwell). Leyendecker dressed up these adorable tykes for a neighborhood Halloween party in 1913—apple bobbing and all. This cuteness is quite the contrast with his Halloween cover ten years later (below).

Witches Night Out by J.C. Leyendecker

Witches Night Out by J.C. Leyendecker October 27, 1923

A creepy witch on a chilly, windy night – and a full harvest moon to illuminate her. Looking at her creepy face (sorry, lady), it is a little difficult to remember that this is the same artist famous for that rakishly handsome, chiseled-featured Arrow Shirt man and the slinky, elegant ladies and gentlemen in the 1920s Kuppenheimer clothing advertisements.

Halloween Fiddler by Norman Rockwell

Halloween Fiddler by Norman Rockwell CG October 22, 1921

A rarely seen Norman Rockwell cover from 1921 shows a fiddler at a Halloween get-together. It must be a lively tune, judging by the way he’s keeping time with a high-stepping foot. Rockwell did 36 covers for the Post’s sister publication, The Country Gentleman.

Lighting the Pumpkin by Eugene Iverd

Lighting the Pumpkin by Eugene Iverd November 3, 1934

This charming cover is from 1934. These kids are ready, dressed in their Halloween best and lighting a giant jack-o’-lantern. Artist Eugene Iverd did many of our best covers of children – see Artist Eugene Iverd’s World of Children, here.

Halloween, 1926 by Edgar Franklin Wittmack

Halloween, 1926 by Edgar Franklin Wittmack October 30, 1926

This well-dressed young man is regretting going to that Halloween party – there is something very scary out there! This creepy cover is from 1926.

Witch’s Mask by Charles Kaiser

Witch's Mask by Charles Kaiser October 31, 1942

In this 1942 cover by artist Charles Kaiser, a little girl is frightened by the view of this witch’s mask through the window – which begs the question: was the witch winking before?